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Chapter 1 Chemical Bonding 1

1.1 Introduction 1

1.2 Atoms,Electrons and Orbitals 1

1.3 Ionic Bonds 3

1.4 Covalent Bonds 4

1.5 Double Bonds and Triple Bonds 5

1.6 Polar Covalent Bonds and Electronegativity 5

1.7 Formal Charge 6

1.8 Structural Formulas of Organic Molecules 6

1.9 Constitutional Isomers 7

1.10 Resonance 7

1.11 The Shapes of Some Simple Molecules 8

1.12 Molecular Dipole Moments 9

1.13 Electron Waves and Chemical Bonds 10

1.14 Bonding in H2:The Valence Bond Model 11

1.15 Bonding in H2:Molecular Orbital Method 12

1.16 Orbital Hybridization and Bonding of Methane 13

1.17 sp3 Hybridization and Bonding of Ethane 14

1.18 sp2 Hybridization and Bonding of Ethylene 14

1.19 sp Hybridization and Bonding of Acetylene 15

1.20 Chapter Summary 16

Review Questions 18

References 20

Chapter 2 Alkanes and Cycloalkanes 21

2.1 Introduction 21

2.2 Structure of Alkanes 22

2.3 Nomenclature of Alkanes 22

2.4 Alkyl Groups 24

2.5 Conformational Isomerization of Alkanes 24

2.6 Physical Properties of Alkanes 27

2.7 Chemical Properties of Alkanes 28

2.8 Cycloalkanes 30

2.9 Chapter Summary 35

Review Questions 36

References 38

Chapter 3 Alkenes and Alkynes 39

3.1 Introduction of Alkenes 39

3.2 Structure of Alkenes 40

3.3 Nomenclature of Alkenes 40

3.4 Physical Properties of Alkenes 42

3.5 Chemical Properties of Alkenes 42

3.6 Dienes 50

3.7 Introduction of Alkynes 54

3.8 Structure of Alkynes 54

3.9 Nomenclature of Alkynes 54

3.10 Physical Properties of Alkynes 55

3.11 Chemical Properties of Alkynes 55

3.12 Chapter Summary 60

Review Questions 61

References 63

Chapter 4 Aromatic Compounds 64

4.1 Introduction 64

4.2 Benzene 65

4.3 Nomenclature of Benzene Derivatives 66

4.4 Physical Properties of Aromatic Hydrocarbon 69

4.5 Chemistry of Benzene Derivatives 70

4.6 Fused-Ring Aronatic Hydrocarbons 80

4.7 Aromaticity and the Hückel Rule 82

4.8 Chapter Summary 84

Review Questions 85

References 88

Chapter 5 Stereochemistry 89

5.1 Introduction 89

5.2 Symmetry Elements 90

5.3 Chiral Carbons 91

5.4 Optical Activity 94

5.5 Configuration of Enantiomers 95

5.6 Isomers with More than One Asymmetric Centers 96

5.7 Chapter Summary 98

Review Questions 98

References 101

Chapter 6 Alkyl Halides 102

6.1 Introduction 102

6.2 Classification 103

6.3 Nomenclature 103

6.4 Reactions of Alkyl Halides 104

6.5 Chapter Summary 111

Review Questions 112

References 115

Chapter 7 Alcohols and Phenols 116

7.1 Introduction 116

7.2 Alcohols 117

7.3 Phenols 124

7.4 Chapter Summary 127

Review Questions 127

References 129

Chapter 8 Ethers,Epoxides,Thiols and Sulfides 130

8.1 Introduction 130

8.2 Nomenclature of Ethers 131

8.3 Structures and Physical Properties of Ethers 132

8.4 Preparations of Ethers 132

8.5 Reactions of Ethers 134

8.6 Crown Ethers 137

8.7 Epoxides 138

8.8 Thiols and Sulfides 142

8.9 Chapter Summary 144

Review Questions 147

References 152

Chapter 9 Aldehydes and Ketones 153

9.1 Introduction 153

9.2 Classification and Nomenclature of Aldehydes and Ketones 154

9.3 Structures of Aldehydes and Ketones 155

9.4 Physical Properties of Aldehydes and Ketones 156

9.5 Chemical Properties of Aldehydes and Ketones 156

9.6 Quinones 174

9.7 Chapter Summary 177

Review Questions 178

References 183

Chapter 10 Carboxylic Acids and Substituted Carboxylic Acids 184

10.1 Introduction 184

10.2 Structure of Carboxylic Acids 184

10.3 Classification of Carboxylic Acids 185

10.4 Nomenclature of Carboxylic Acids 185

10.5 Chemical Properties and Reactions of Carboxylic Acids 186

10.6 Substituted Carboxylic Acids 192

10.7 Chapter Summary 194

Review Questions 195

References 198

Chapter 11 Carboxylic Acid Derivatives 199

11.1 Introduction 199

11.2 Acyl Halides 200

11.3 Acid Anhydrides 202

11.4 Esters 203

11.5 Amides 206

11.6 Urea 207

11.7 The Claisen Condensation 208

11.8 Chapter Summary 209

Review Questions 209

References 212

Chapter 12 Amines 213

12.1 Introduction 213

12.2 Nomenclature of Amines 214

12.3 Physical Properties of Amines 215

12.4 Synthesis of Amines 215

12.5 Reactions of Amines 218

12.6 Reactions of Arenediazonium Salts 221

12.7 Diazonium Coupling Reaction 223

12.8 Chapter Summary 223

Review Questions 223

References 226

Chapter 13 Aromatic Heterocycles 227

13.1 Introduction 227

13.2 Classification and Nomenclature of Heterocycles 228

13.3 Five-Membered Heterocycles 229

13.4 Chapter Summary 240

Review Questions 240

References 242

Chapter 14 Carbohydrates 243

14.1 Introduction 243

14.2 Conformations of Sugars 246

14.3 Polyfunctional Chemistry of Sugars 251

14.4 Complex Sugars in Nature 253

14.5 Chapter Summary 256

Review Questions 257

References 258

Chapter 15 Lipids 259

15.1 Introduction 259

15.2 Triglycerides 259

15.3 Phospholipids 262

15.4 Steroids 263

15.5 Chapter Summary 264

Review Questions 265

References 268

Index 269